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Your Chepstow Vacation
When a city break is calling, answer it with a vacation package to Chepstow. The neighborhood of Trellech United, which is great for culture, nature and history, makes a fantastic base for your adventures. If your trip to Chepstow includes some sightseeing, visit renowned attractions like Chepstow Racecourse, Tintern Abbey and Chepstow Castle. Expedia has what you need to escape your routine. Tailor your vacation to Chepstow to match your travel style, whatever that may look like.
The Latest Chepstow vacation packages
Price found within the past 48 hours. Click for updated prices.



4 Berkeley Sq - YourApartment
$1,430
per person
Dec 4 - Dec 10
just found
Roundtrip non-stop flight included
Washington (IAD) to Bristol (BRS)
7.6/10 Good! (70 reviews)
The building was in a great location. a nice quiet square, just 5 minutes from the start of all the bars and restaurants.
The room itself was nothing like the pictures. It was one small room only which contained the shower and the sink. there was no wardrobe or cupboard to put clothes and shoes. There was a single rail attached to a roof beam which had 6 clothes hangers.
The most alarming problem, was the fact that there was no toilet. This was located on the landing which needed a separate key to open. This is not ideal when you wake up during the night and its dark and you need to locate the key before you can use the toilet.
The room we was allocated, but looked nothing like the pictures, was located at the top of the building. Apparently, it was on the 3rd floor. But to get there, you had to walk up 5 small staircases, 55 steps in total.
When we arrived, i did complain about the room and we was offered a different one in the basement, as long as we had used nothing in the room. Unfortunately in the 2 hours between sending my complaint and receiving the reply, we had unpacked and showered, rendering the room used.
For the money we paid, the minimum you expect is an en-suite toilet.
Reviewed on Apr 27, 2026

Clifton Hotel
Clifton
$1,373
per person
Dec 3 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Washington (IAD) to Bristol (BRS)
7.4/10 Good! (1,003 reviews)
The property is located in a nice area of the town , but overall the amenities and the rooms are centuries old. If you need a a place to crash out after a bender it would be suitable because you won’t feel the cold. The rooms are so tiny and the king size bed is two singles put together. For the price I paid I would have went to a premier in or travel lodge as they would be a class above this hotel.
Staff are nice and friendly and the hotel is clean.
No bathtub, no air con, no double glazing !
Heating is not turned on until 7pm, had to go to reception to request it.
Reviewed on Oct 17, 2026

Hotel Collingwood, BW Signature Collection
Bournemouth City Centre
$1,252
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Bristol (BRS)
8.2/10 Very Good! (748 reviews)
The hotel was clean but you can tell it is ready for a refurbishment. In the top floor room that I was in I could hear the road noise very loudly as if the window was open which it was not. In the bathroom one of the floor tiles had no grout in it. The carpets were slightly stained and paint work all scratched in the room. The door did not fully fit the frame so when going to sleep you could see lots of light from the hallway. The staff were lovely as was the food in the restaurant.
Reviewed on Oct 16, 2026
Stay near popular Chepstow attractions

Tintern Abbey
9.6/10 (60 reviews)
Tour the ruins of an ancient monastery where Cistercian monks used to live, pray and study. See the remains of their former dwellings and church.
Photo by Miguel Vasquez
Chepstow Castle
9.0/10 (29 reviews)
Chepstow Castle is the oldest surviving stone fort in Britain and easily one of the most spectacular castles in Wales. The impressive castle dates back to the Norman invasion and perches precariously atop a cliff on the banks of the River Wye. Any visit is sure to invoke plenty of awe and wonder.
Chepstow Racecourse
9.0/10 (26 reviews)
Chepstow Racecourse is situated in Monmouthshire in south-east Wales, near the southern end of the Wye Valley. The track is a great point of interest in the UK and attracts visitors from all over the world.
St. Pierre Country Club
7.6/10 (17 reviews)
Enjoy a round of golf in Mathern at St. Pierre Country Club. Check out the shops and top-notch restaurants in this walkable area.
Symonds Yat Rock
9.6/10 (7 reviews)
Commune with nature and explore the great outdoors at Symonds Yat Rock during your travels in Tidenham. Make time for the spas and golf courses in this family-friendly area.
Caerwent Roman Town
6.0/10 (2 reviews)
You can learn about the history of Newport with a trip to Caerwent Roman Town. Make time for the spas and golf courses in this relaxing area.
Dewstow Golf Club
Enjoy a round of golf in Newport at Dewstow Golf Club. Check out the spas and top-notch restaurants in this quaint area.
Parva Farm Vineyard
10.0/10 (2 reviews)
You can enjoy a tasting or tour at Parva Farm Vineyard during your travels to Tintern. Check out the spas and top-notch restaurants in this relaxing area.
What to do in Chepstow

Cardiff: South Wales Cliffs, Beaches & Castles Day Tour
$107
per adult
Chepstow Hotel Deals

Delta Hotels by Marriott St. Pierre Country Club
St Pierre Park Chepstow Wales
Fully refundableReserve now, pay when you stay
$103 nightly
$124 total
Nov 8 - Nov 9
Total with taxes and fees

Delta Hotels by Marriott Bristol City Centre
2 Lower Castle Street Bristol England
Fully refundableReserve now, pay when you stay
$75 nightly
$90 total
Nov 8 - Nov 9
Total with taxes and fees

Clayton Hotel Bristol City
Broad Street Bristol England
Fully refundableReserve now, pay when you stay
$96 nightly
$116 total
Oct 25 - Oct 26
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find the Best Chepstow Vacation Packages
Chepstow Essential Information
Language | Welsh |
|---|---|
Currency | British pounds sterling |
Population | 16,200 |
Max Temp Winter | 45ºF |
Max Temp Summer | 65ºF |
Top Sights | Chepstow Castle, Chepstow Castle and Caldicot Castle |
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Frequently asked questions
How much does a Chepstow vacation package cost?
Offering excellent value package deals from $1,018 on Expedia, you'll be thrilled with how little a vacation to Chepstow costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chepstow?
If you'd like to snag a cheap Chepstow vacation package, consider traveling in August, November and December. You'll usually find lower prices on accommodations and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Chepstow?
We recommend booking a Chepstow vacation for a minimum of 2 days. This will allow you enough time to check off major attractions such as Chepstow Museum and Parva Farm Vineyard, and also explore neighborhoods like Portskewett and Devauden. You might even be able to fit in a day trip (or two) from Chepstow.
Is it worth booking a vacation package to Chepstow?
From attractions such as Chepstow Racecourse and Chepstow Castle to its epic history, a Chepstow vacation offers a vibrant mix of experiences. With so much to do and see, it's time to find out for yourself why Chepstow is such a good vacation destination.
How to find the best Chepstow package deals?
Use Expedia's filters to help you find some unbeatable Chepstow package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Chepstow package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Chepstow vacation as a package?
You can enjoy significant savings on your Chepstow escape by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chepstow?
If you're considering a spontaneous Chepstow getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Chepstow?
- Choose when to go: Check your calendar and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to escape to Chepstow.
- Calculate your budget: Make sure you have enough money to cover everything from dining out and transportation to flights and activities. Your accommodations will probably be the biggest expense during your trip to Chepstow.
- Use Expedia's trip planning tool to explore Chepstow: Research every aspect of your trip to Chepstow with this handy planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings.
- Decide how long to go for: Now that you're more familiar with Chepstow, you can work out the ideal length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to do.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Chepstow vacation package.
- Book experiences or activities in advance: Whether it's entrance to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of Chepstow. Find all the fun things to do in Chepstow with our dedicated travel guide.
Does Expedia offer Book Now, Pay Later Chepstow vacation packages?
Set off on your dream escape to Chepstow with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait for your next payday — we've teamed up with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snap up travel deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.





















